TY  - JOUR
A1  - Zhang, Fangyuan
A1  - Radacki, Krzysztof
A1  - Braunschweig, Holger
A1  - Lambert, Christoph
A1  - Ravat, Prince
T1  - Zinc-[7]helicenocyanine and its discrete π-stacked homochiral Dimer
JF  - Angewandte Chemie International Edition
N2  - In this communication, we demonstrate a novel approach to prepare a discrete dimer of chiral phthalocyanine (Pc) by exploiting the flexible molecular geometry of helicenes, which enables structural interlocking and strong aggregation tendency of Pcs. Synthesized [7]helicene-Pc hybrid molecular structure, zinc-[7]helicenocyanine (Zn-7HPc), exclusively forms a stable dimeric pair consisting of two homochiral molecules. The dimerization constants were estimated to be as high as 8.96×10\(^6\) M\(^{−1}\) and 3.42×107 M\(^{−1}\) in THF and DMSO, respectively, indicating remarkable stability of dimer. In addition, Zn\(^{-7}\)HPc exhibited chiral self-sorting behavior, which resulted in preferential formation of a homochiral dimer also in the racemic sample. Two phthalocyanine subunits in the dimeric form strongly communicate with each other as revealed by a large comproportionation constant and observation of an IV-CT band for the thermodynamically stable mixed-valence state.
KW  - organic chemistry
KW  - supramolecular assembly
KW  - chirality
KW  - helicenes
KW  - homochiral dimer
KW  - phthalocyanines
Y1  - 2021
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-256534
VL  - 60
ER  -